Benzoylacetonitrile → 2-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrile

Participants

Reaction Steps

A solution of 3-oxo-3-phenylpropanenitrile (1.0 equiv.) in 1,1-dimethoxy-N,N-dimethylmethanamine (2.2 M) was stirred at 50° C. under nitrogen overnight. After reaction completion, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (30% ethyl acetate in petroleum ether) to afford 2-benzoyl-3-(dimethylamino)acrylonitrile (8% yield) as a yellow oil. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 7.83 (s, 1H), 7.61-7.60 (m, 2H), 7.52-7.50 (m, 1H), 7.47-7.45 (m, 2H), 3.37 (s, 3H), 3.28 (s, 3H); MS (ESI) m/z=201.2 [M+1]+.

Provenance & Evidence